JP2016514709A5 - - Google Patents
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- JP2016514709A5 JP2016514709A5 JP2016503521A JP2016503521A JP2016514709A5 JP 2016514709 A5 JP2016514709 A5 JP 2016514709A5 JP 2016503521 A JP2016503521 A JP 2016503521A JP 2016503521 A JP2016503521 A JP 2016503521A JP 2016514709 A5 JP2016514709 A5 JP 2016514709A5
- Authority
- JP
- Japan
- Prior art keywords
- oxo
- dihydro
- amino
- pyrazolo
- pyridin
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
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- -1 aminocarbonyloxy Chemical group 0.000 claims 321
- 125000000217 alkyl group Chemical group 0.000 claims 177
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 151
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 53
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims 46
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 35
- WEVYAHXRMPXWCK-UHFFFAOYSA-N acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims 25
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 21
- 125000003118 aryl group Chemical group 0.000 claims 18
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 17
- 125000003277 amino group Chemical compound 0.000 claims 17
- 125000001072 heteroaryl group Chemical group 0.000 claims 16
- 125000005153 alkyl sulfamoyl group Chemical group 0.000 claims 15
- 150000007960 acetonitrile Chemical compound 0.000 claims 14
- 125000003282 alkyl amino group Chemical group 0.000 claims 14
- 150000001875 compounds Chemical class 0.000 claims 14
- 125000004501 isothiazol-5-yl group Chemical group S1N=CC=C1* 0.000 claims 12
- 208000006673 Asthma Diseases 0.000 claims 11
- MQAYFGXOFCEZRW-UHFFFAOYSA-M oxane-2-carboxylate Chemical compound [O-]C(=O)C1CCCCO1 MQAYFGXOFCEZRW-UHFFFAOYSA-M 0.000 claims 11
- 239000008194 pharmaceutical composition Substances 0.000 claims 11
- 125000004404 heteroalkyl group Chemical group 0.000 claims 10
- 125000000753 cycloalkyl group Chemical group 0.000 claims 9
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 9
- 150000003839 salts Chemical class 0.000 claims 9
- 239000011780 sodium chloride Substances 0.000 claims 9
- 125000006652 (C3-C12) cycloalkyl group Chemical group 0.000 claims 8
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 8
- 201000010099 disease Diseases 0.000 claims 7
- DNUTZBZXLPWRJG-UHFFFAOYSA-M piperidine-1-carboxylate Chemical compound [O-]C(=O)N1CCCCC1 DNUTZBZXLPWRJG-UHFFFAOYSA-M 0.000 claims 7
- 125000004966 cyanoalkyl group Chemical group 0.000 claims 6
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 6
- 229910052736 halogen Inorganic materials 0.000 claims 6
- 150000002367 halogens Chemical class 0.000 claims 6
- 125000004043 oxo group Chemical group O=* 0.000 claims 6
- 125000004482 piperidin-4-yl group Chemical compound N1CCC(CC1)* 0.000 claims 6
- 125000001424 substituent group Chemical group 0.000 claims 6
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 5
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 5
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims 4
- 125000003349 3-pyridyl group Chemical compound N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 4
- 206010003246 Arthritis Diseases 0.000 claims 4
- 206010003816 Autoimmune disease Diseases 0.000 claims 4
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims 4
- 125000003545 alkoxy group Chemical group 0.000 claims 4
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims 4
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims 4
- 125000004429 atoms Chemical group 0.000 claims 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims 4
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 4
- 229910052757 nitrogen Inorganic materials 0.000 claims 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 4
- VZIHTQKMHLOIII-UHFFFAOYSA-N 3,5-dihydro-2H-furan Chemical compound [CH]1CCOC1 VZIHTQKMHLOIII-UHFFFAOYSA-N 0.000 claims 3
- 102100019517 JAK1 Human genes 0.000 claims 3
- 101700034277 JAK1 Proteins 0.000 claims 3
- 102100019516 JAK2 Human genes 0.000 claims 3
- 101700016050 JAK2 Proteins 0.000 claims 3
- 241000124008 Mammalia Species 0.000 claims 3
- 125000004442 acylamino group Chemical group 0.000 claims 3
- 229910052799 carbon Inorganic materials 0.000 claims 3
- 125000004672 ethylcarbonyl group Chemical group [H]C([H])([H])C([H])([H])C(*)=O 0.000 claims 3
- 229910052739 hydrogen Inorganic materials 0.000 claims 3
- 230000002401 inhibitory effect Effects 0.000 claims 3
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims 3
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 3
- PTRJHYDRYXRGEL-UHFFFAOYSA-N 2,3,5,6-tetrahydropyran Chemical compound [CH]1CCOCC1 PTRJHYDRYXRGEL-UHFFFAOYSA-N 0.000 claims 2
- RZXQUPPXEYSAEP-UHFFFAOYSA-N C(#N)CC1(CCN(CC1)CC1=CC=C(C=C1)C(C)C)N1N=C(C=2C(NC=CC21)=O)NC2=CC=C(C=C2)S(=O)(=O)N(C)C Chemical compound C(#N)CC1(CCN(CC1)CC1=CC=C(C=C1)C(C)C)N1N=C(C=2C(NC=CC21)=O)NC2=CC=C(C=C2)S(=O)(=O)N(C)C RZXQUPPXEYSAEP-UHFFFAOYSA-N 0.000 claims 2
- ULWWEPNVLQCJFW-UHFFFAOYSA-N CC1CCCCN1C(=O)c1ccc(Nc2nn(c3cc[nH]c(=O)c23)C2(CC#N)CCCOC2)cc1C Chemical compound CC1CCCCN1C(=O)c1ccc(Nc2nn(c3cc[nH]c(=O)c23)C2(CC#N)CCCOC2)cc1C ULWWEPNVLQCJFW-UHFFFAOYSA-N 0.000 claims 2
- ZVMGSKOXDHVBRG-UHFFFAOYSA-N CN(C)S(=O)(=O)c1ccc(Nc2nn(c3cc[nH]c(=O)c23)C2(CC#N)CCCCC2F)cc1 Chemical compound CN(C)S(=O)(=O)c1ccc(Nc2nn(c3cc[nH]c(=O)c23)C2(CC#N)CCCCC2F)cc1 ZVMGSKOXDHVBRG-UHFFFAOYSA-N 0.000 claims 2
- PMYPCZQHBIQDAK-UHFFFAOYSA-N COC1CCN(C1)C(=O)c1ccc(Nc2nn(c3cc[nH]c(=O)c23)C2(CC#N)CCCOC2)cc1C Chemical compound COC1CCN(C1)C(=O)c1ccc(Nc2nn(c3cc[nH]c(=O)c23)C2(CC#N)CCCOC2)cc1C PMYPCZQHBIQDAK-UHFFFAOYSA-N 0.000 claims 2
- 102000008986 Janus Human genes 0.000 claims 2
- 108050000950 Janus Proteins 0.000 claims 2
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims 2
- 150000001408 amides Chemical class 0.000 claims 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 2
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 2
- 101710044204 cyp165C4 Proteins 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 claims 2
- 125000006260 ethylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])C([H])([H])[H] 0.000 claims 2
- 239000001257 hydrogen Substances 0.000 claims 2
- 125000004435 hydrogen atoms Chemical class [H]* 0.000 claims 2
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims 2
- 125000005928 isopropyloxycarbonyl group Chemical group [H]C([H])([H])C([H])(OC(*)=O)C([H])([H])[H] 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims 2
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims 2
- 125000004458 methylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])[H] 0.000 claims 2
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims 2
- 230000000414 obstructive Effects 0.000 claims 2
- 229910052760 oxygen Inorganic materials 0.000 claims 2
- OEUAEFQARUZYLW-UHFFFAOYSA-N prop-1-en-2-olate Chemical group [CH2+]C([O-])=C OEUAEFQARUZYLW-UHFFFAOYSA-N 0.000 claims 2
- 229910052717 sulfur Inorganic materials 0.000 claims 2
- NLOLSXYRJFEOTA-OWOJBTEDSA-N (E)-1,1,1,4,4,4-hexafluorobut-2-ene Chemical compound FC(F)(F)\C=C\C(F)(F)F NLOLSXYRJFEOTA-OWOJBTEDSA-N 0.000 claims 1
- IEKYYCCJMBUIFV-UHFFFAOYSA-N 1,3$l^{2}-thiazolidin-2-ylidenemethanone Chemical group O=C=C1[N]CCS1 IEKYYCCJMBUIFV-UHFFFAOYSA-N 0.000 claims 1
- KOFZWWMCDUHEEM-UHFFFAOYSA-N 1-methylpyrrolidine Chemical group [CH2]N1CCCC1 KOFZWWMCDUHEEM-UHFFFAOYSA-N 0.000 claims 1
- 125000004343 1-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims 1
- QUSIJPWIXLGKNS-UHFFFAOYSA-M 3,3-dimethylbut-1-en-1-olate Chemical group CC(C)(C)[C-]=C[O-] QUSIJPWIXLGKNS-UHFFFAOYSA-M 0.000 claims 1
- 125000001255 4-fluorophenyl group Chemical compound [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 1
- POOPWPIOIMBTOH-UHFFFAOYSA-N 8-oxa-3-azabicyclo[3.2.1]octane Chemical compound C1NCC2CCC1O2 POOPWPIOIMBTOH-UHFFFAOYSA-N 0.000 claims 1
- 208000000884 Airway Obstruction Diseases 0.000 claims 1
- 206010006451 Bronchitis Diseases 0.000 claims 1
- UVKCEETVNJEFST-UHFFFAOYSA-N C(#N)CC(=O)N1CCC(CC1)(CC#N)N1N=C(C=2C(NC=CC21)=O)NC2=CC=C(C=C2)S(=O)(=O)N(C)C Chemical compound C(#N)CC(=O)N1CCC(CC1)(CC#N)N1N=C(C=2C(NC=CC21)=O)NC2=CC=C(C=C2)S(=O)(=O)N(C)C UVKCEETVNJEFST-UHFFFAOYSA-N 0.000 claims 1
- FPYHDWUSAOFILC-UHFFFAOYSA-N C(#N)CC1(C(CN(CC1)C(=O)OC(C)(C)C)F)N1N=C(C=2C(NC=CC21)=O)NC2=CC=C(C=C2)S(N(C)C)(=O)=O Chemical compound C(#N)CC1(C(CN(CC1)C(=O)OC(C)(C)C)F)N1N=C(C=2C(NC=CC21)=O)NC2=CC=C(C=C2)S(N(C)C)(=O)=O FPYHDWUSAOFILC-UHFFFAOYSA-N 0.000 claims 1
- TWNHDYRZRRWJBV-UHFFFAOYSA-N C(#N)CC1(CCC(CC1)N1CC(C1)F)N1N=C(C=2C(NC=CC21)=O)NC2=CC=C(C=C2)S(=O)(=O)N(C)C Chemical compound C(#N)CC1(CCC(CC1)N1CC(C1)F)N1N=C(C=2C(NC=CC21)=O)NC2=CC=C(C=C2)S(=O)(=O)N(C)C TWNHDYRZRRWJBV-UHFFFAOYSA-N 0.000 claims 1
- HTCAIMKNUSQAOW-UHFFFAOYSA-N C(#N)CC1(CCCC1)N1N=C(C=2C(NC=CC21)=O)NC2=CC=C(C=C2)S(=O)(=O)N(C)C(C(=O)OC(C)(C)C)(C)C Chemical compound C(#N)CC1(CCCC1)N1N=C(C=2C(NC=CC21)=O)NC2=CC=C(C=C2)S(=O)(=O)N(C)C(C(=O)OC(C)(C)C)(C)C HTCAIMKNUSQAOW-UHFFFAOYSA-N 0.000 claims 1
- YOFVFRHRYLERED-UHFFFAOYSA-N C(#N)CC1(CCCC1)N1N=C(C=2C(NC=CC21)=O)NC=2C=C1CN(C(C1=CC2)=O)C(C(=O)OC(C)(C)C)(C)C Chemical compound C(#N)CC1(CCCC1)N1N=C(C=2C(NC=CC21)=O)NC=2C=C1CN(C(C1=CC2)=O)C(C(=O)OC(C)(C)C)(C)C YOFVFRHRYLERED-UHFFFAOYSA-N 0.000 claims 1
- CABBRDBQABPNGW-UHFFFAOYSA-N C(#N)CC1(CCN(CC1)C(=O)C12CC3CC(CC(C1)C3)C2)N2N=C(C=3C(NC=CC32)=O)NC3=CC=C(C=C3)S(=O)(=O)N(C)C Chemical compound C(#N)CC1(CCN(CC1)C(=O)C12CC3CC(CC(C1)C3)C2)N2N=C(C=3C(NC=CC32)=O)NC3=CC=C(C=C3)S(=O)(=O)N(C)C CABBRDBQABPNGW-UHFFFAOYSA-N 0.000 claims 1
- AWGKAUGOFYHMOH-UHFFFAOYSA-N C(#N)CC1(CCN(CC1)C(=O)C1=CC=CC=C1)N1N=C(C=2C(NC=CC=21)=O)NC1=CC=C(C=C1)S(=O)(=O)N(C)C Chemical compound C(#N)CC1(CCN(CC1)C(=O)C1=CC=CC=C1)N1N=C(C=2C(NC=CC=21)=O)NC1=CC=C(C=C1)S(=O)(=O)N(C)C AWGKAUGOFYHMOH-UHFFFAOYSA-N 0.000 claims 1
- GDRZQMCCVIQSNV-UHFFFAOYSA-N C(#N)CC1(CCN(CC1)C(=O)C1CCCCC1)N1N=C(C=2C(NC=CC21)=O)NC2=CC=C(C=C2)S(=O)(=O)N(C)C Chemical compound C(#N)CC1(CCN(CC1)C(=O)C1CCCCC1)N1N=C(C=2C(NC=CC21)=O)NC2=CC=C(C=C2)S(=O)(=O)N(C)C GDRZQMCCVIQSNV-UHFFFAOYSA-N 0.000 claims 1
- HEGJPWPZJCJTQQ-UHFFFAOYSA-N C(#N)CC1(CCN(CC1)C(C(C)(C)C)=O)N1N=C(C=2C(NC=CC=21)=O)NC1=CC=C(C=C1)S(=O)(=O)N(C)C Chemical compound C(#N)CC1(CCN(CC1)C(C(C)(C)C)=O)N1N=C(C=2C(NC=CC=21)=O)NC1=CC=C(C=C1)S(=O)(=O)N(C)C HEGJPWPZJCJTQQ-UHFFFAOYSA-N 0.000 claims 1
- DUNJENCVBYFJMC-UHFFFAOYSA-N C(#N)CC1(CCN(CC1)C(C)C1=C(C=CC=C1F)F)N1N=C(C=2C(NC=CC21)=O)NC2=CC=C(C=C2)S(=O)(=O)N(C)C Chemical compound C(#N)CC1(CCN(CC1)C(C)C1=C(C=CC=C1F)F)N1N=C(C=2C(NC=CC21)=O)NC2=CC=C(C=C2)S(=O)(=O)N(C)C DUNJENCVBYFJMC-UHFFFAOYSA-N 0.000 claims 1
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- XBJLPFNXTWOBQS-UHFFFAOYSA-N C(#N)CC1(CCN(CC1)C(CC(C)(C)C)=O)N1N=C(C=2C(NC=CC=21)=O)NC1=CC=C(C=C1)S(=O)(=O)N(C)C Chemical compound C(#N)CC1(CCN(CC1)C(CC(C)(C)C)=O)N1N=C(C=2C(NC=CC=21)=O)NC1=CC=C(C=C1)S(=O)(=O)N(C)C XBJLPFNXTWOBQS-UHFFFAOYSA-N 0.000 claims 1
- DQOSTQVAQJUSJW-UHFFFAOYSA-N C(#N)CC1(CCN(CC1)C(CC)=O)N1N=C(C=2C(NC=CC21)=O)NC2=CC=C(C=C2)S(=O)(=O)N(C)C Chemical compound C(#N)CC1(CCN(CC1)C(CC)=O)N1N=C(C=2C(NC=CC21)=O)NC2=CC=C(C=C2)S(=O)(=O)N(C)C DQOSTQVAQJUSJW-UHFFFAOYSA-N 0.000 claims 1
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- JWZIADYHSJEHSW-UHFFFAOYSA-N C(#N)CC1(CCN(CC1)C1=NC=C(C#N)C=C1)N1N=C(C=2C(NC=CC21)=O)NC2=CC=C(C=C2)S(=O)(=O)C Chemical compound C(#N)CC1(CCN(CC1)C1=NC=C(C#N)C=C1)N1N=C(C=2C(NC=CC21)=O)NC2=CC=C(C=C2)S(=O)(=O)C JWZIADYHSJEHSW-UHFFFAOYSA-N 0.000 claims 1
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| WO2011130146A1 (en) * | 2010-04-14 | 2011-10-20 | Array Biopharma Inc. | 5, 7-substituted-imidazo [1, 2-c] pyrimidines as inhibitors of jak kinases |
| US20130303533A1 (en) | 2010-09-01 | 2013-11-14 | Ambit Biosciences Corporation | Azolopyridine and azolopyrimidine compounds and methods of use thereof |
| CN103313987A (zh) * | 2010-11-19 | 2013-09-18 | 弗·哈夫曼-拉罗切有限公司 | 吡唑并吡啶化合物、吡唑并吡啶化合物以及它们作为tyk2抑制剂的用途 |
| BR112013025142A2 (pt) * | 2011-04-01 | 2019-09-24 | Univ Utah Res Found | análogos de 3-(1h-benzo{d}imidazol-2-il)-1h-indazol substituído como inibidores da cinase pdk1 |
| UA111854C2 (uk) * | 2011-09-07 | 2016-06-24 | Інсайт Холдінгс Корпорейшн | Способи і проміжні сполуки для отримання інгібіторів jak |
| US8962608B2 (en) * | 2011-09-22 | 2015-02-24 | Merck Sharp & Dohme Corp. | Cycloalkylnitrile pyrazole carboxamides as janus kinase inhibitors |
| WO2013180265A1 (ja) * | 2012-06-01 | 2013-12-05 | 武田薬品工業株式会社 | 複素環化合物 |
| WO2013192125A1 (en) * | 2012-06-20 | 2013-12-27 | Merck Sharp & Dohme Corp. | Pyrazolyl derivatives as syk inhibitors |
-
2013
- 2013-03-19 WO PCT/CN2013/072873 patent/WO2014146249A1/en active Application Filing
-
2014
- 2014-03-19 JP JP2016503521A patent/JP2016514709A/ja active Pending
- 2014-03-19 CA CA2901765A patent/CA2901765A1/en not_active Abandoned
- 2014-03-19 EP EP14770170.0A patent/EP2976339B1/en active Active
- 2014-03-19 WO PCT/CN2014/000297 patent/WO2014146491A1/en active Application Filing
- 2014-03-19 RU RU2015144485A patent/RU2664533C2/ru not_active IP Right Cessation
- 2014-03-19 US US14/778,046 patent/US9957264B2/en active Active
- 2014-03-19 BR BR112015023858A patent/BR112015023858A2/pt not_active Application Discontinuation
- 2014-03-19 AU AU2014234907A patent/AU2014234907B2/en not_active Ceased
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP7278649B2 (ja) | 2019-01-30 | 2023-05-22 | 格格巫（珠海）生物科技有限公司 | Ｊａｋ阻害剤及びその製造方法 |
| JP7278649B6 (ja) | 2019-01-30 | 2024-02-15 | 格格巫（珠海）生物科技有限公司 | Ｊａｋ阻害剤及びその製造方法 |
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